So do I need to open port 389 on the VPS to get Outlook to work at all? Is there anything else I need to do serverside? Anything I should know about Outlook (I remember when setting up postfix+dovecot from scratch one time there were configs that needed to be set in order for Outlook to work, but I'm not sure what the iRedMail default configs are like, i.e. if they are Outlook-friendly, though I should learn).

Re: Configure Outlook to use iRedMail accounts

Ok, thanks. I've got it working with Outlook 2007. But I need to be able to use it with Outlook 2003. The problem is that Outlook 2003 doesn't support TLS. So is there a way to get iredmail to accept SSL instead of TLS for sending from a client?

I guess even to disable tls altogether is an option if it will get Outlook 2003 to work. I've tried modifying postfix's main.cf to have,

smtpd_use_tls=noandsmtpd_tls_security_level = none

But this still doesn't work when I set the encryption method to "None" in Outlook. Man, I hate Outlook.

Re: Configure Outlook to use iRedMail accounts

I've been looking around further, and it seems like it might work to use SSL over port 465, but this is deprecated and not supported by iRedMail out-of-the-box (I think). Is there any workaround to get iRedMail to use SSL over port 465 for smtp?

The other option is to disable encryption altogether, but I can't seem to figure that out either. I tried commenting out all the tls-related lines in /etc/postfix/main.cf and reloading postfix. Then in Outlook I tried smtp port 25 with No encryption, but it's still not working. But I've found that even with this configuration, I can't connect via POP3 without using SSL in Outlook, so I don't think I'm disabling the encryption stuff in postfix correctly.

Here's my main.cf in an attempt to disable tls/ssl and use port 25 with no encryption.